How do you know it’s time?

When it's not fun or at least you don't enjoy it anymore and you'd rather be doing something else.

I'm not a head guy and I'm only 8 years in, but our head coach went through this same feeling a couple years ago - this is year 31 or something like that for him, with the last 19 being the head guy

We had a 5 very successful but very stressful seasons in a row. A lot of behind the scenes BS, plus dealing with covid crap for almost a year and a half. His son graduated and was going to play college football so he thought he might hang it up at least temporarily and just follow his son's team. Our season ended in the state-semi's, which is the week of Thanksgiving for us. From the first week of December to the first week of February he completely cut everything football related out for a while. Told all of us assistants he was going to take some time to decide what he'd do and we all obviously told him to go ahead. After his couple months without thinking about it every day he decided to come back for at least a year. That was 2 years ago now and he's told me several times he's had more fun in the last 2 years than he did in the previous 10. Now all the time he's talking about what we're going to do in the future, looking ahead to improvements we want to make to our facilities & equipment, talking about upcoming 7th & 8th grade classes, etc. He's excited about all of it again

Moral of the story - make it through this season and then give yourself a good amount of time off before you make a decision. Last thing you want to do is rush into a decision within weeks of the season ending and regret it 

i could be wrong, as i've never been one, so take this for what it's worth, (which is basically nothing)-
but i would think admin would burn you out worse than coaching.

but i have a low tolerance for bs, and i think that's pretty much all administration is.
better paycheck, though.

i'm an assistant this year for the 1st time in 9 years...having a great time. Sometimes you just need a change.

not disagreeing here.
actually, i kind of agree.

but it got me to thinking.
i don't remember ever having a job that wasn't a hassle, coaching or otherwise.

maybe because i'm not a social person, but i had a family to take care of, so sometimes you just have to bite the bullet and do what you have to.
if you have options, that's a good thing. i never had many.

but i have to say, bullets taste like crap.
and they're hard on your teeth.

When it becomes something you don't look forward to anymore it's time to get out. For some of us that could be as short (or shorter) than 10 years. For others it can be as long (or longer) than 50 years. A lot depends upon your own goals and processes. Coaching football was NOT in my original plan for my life. For me it started out when my old HS coach asked me if I would be interested in helping coach the freshman team when an injury forced me out of playing in college. ESPN had just started and as a journalism major I thought working for those guys would be a great career path for the future. Long story short. After a season of coaching I was hooked. Changed my major to PE because in those days most coaches were PE teachers. I was a HS assistant, a HS DC, a college assistant, a college DC, a HS HC, a HS AD, a HS Dean, and a HS AP. 49 years later I retired. At my age the grind just became too much. Didn't have the passion anymore (or the patience) for practices, parents, and principals. Yes, I miss Friday nights, and the interactive relationships I had with the kids, but not much else. My Friday nights are now on Saturdays in front of the TV critiquing college coaches.

I gave up high school ball for the middle school level a couple of times to catch a breath. But, I've given it up at this point. I knew it was time when I had to wind myself up for practice in the beginning of September. I always loved practice because I loved the teaching aspect of coaching. I knew I was fried when I didn't enjoy that anymore.

I took a step back and did middle school. It's fun and I don't have pressure to win. I did give up middle school and high school wrestling. I got tired of kids saying they are the {censored} then crying when they lose a match.